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Most Insta-Worthy Spots in Winter Garden

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Hunting down the perfect photo spot can be tough, but not in Winter Garden. Walking the streets of this beautiful city, you’re guaranteed to stumble upon  some insta-worthy places. Whether you’re dreaming of a photo-filled day with friends or you’re just looking to spice up your Instagram feed, Winter Garden is calling your name. 

Grab your camera, your crew, and have this photo guide handy. It’s time to check out Winter Garden’s most instagrammable locations. 

City Hall

Being one of the first buildings you see driving into Downtown Winter Garden, you can’t miss The City Hall. The neutral building, surrounded by pop-of-color flowers and trees, makes for a staple photo location. Whether you stand in front of the stunning building or sit along the fountain and flowers, you can’t go wrong. 

📍 300 W Plant St, Winter Garden, FL 34787

More Space House

If farmhouse vibes are your thing, you’ll want to add the More Space House to the top of your list of Insta-worthy Winter Garden locations. From the white shiplap walls to the wooden rocking chairs on the porch, photo opportunities here are endless. 

📍 446 W Plant St, Winter Garden, FL 34787

Park Place

Get creative by turning unconventional places into Insta-worthy photo location, like Park Place. This beautiful town home community in Winter Garden is surrounded by lush greenery and brick walls. The secluded location gives you the freedom to play around with different background and angles away from the hustle and bustle of Downtown. 

📍 462 W Plant St, Winter Garden, FL 34787

The Garden Theater is a refurbished, historic space where you can see a performance and take top-notch photos for your Instagram. The red and green vintage theater sign makes for a stunning backdrop, both during the day and at night.

📍 160 W Plant St, Winter Garden, FL 34787

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Winter Garden Arch

The Winter Garden clock tower arch, located on at the intersection of Plant Street and Main Street, is by far one of the most popular photo locations. And we can tell why! The combination of the large clock, “Winter Garden” sign, and the surrounding flowers makes it the perfect spot for tourists and locals to snap pictures.

After snapping a few images here, continue walking down Orange Trail to find other Insta-worthy photo spots. 

📍 N Main St. Winter Garden, FL 34787

Green Wood Wall

Simple doesn’t have to mean boring, especially when it comes to this green wood wall in Downtown Winter Garden. The faded green wood adds a colorful and vintage touch to every image. Making it the perfect photo opt for those looking to trade city vibes for a more rustic, small town feel. 

📍 33 State Hwy 537 Winter Garden, FL 34787

Grey Blue Metal Wall

The secret to taking eye-catching Instagram photos is simply standing in front of a textured wall. This grey blue metal wall is a simple color, but the textured metal adds a fun, rustic vibe to any photo. If you’re tired of the same old spots, this is a must stop on your next photo outing. 

📍 28 N Main St. Winter Garden, FL 34787

The Edgewater Hotel

The Edgewater Hotel is a historic inn that will fully transport you back in time to the 1920’s. From the lush greenery to the brick walls,  it’s impossible to take a “bad photo” at this Insta-worthy  location. 

📍 99 W Plant St, Winter Garden, FL 34787

Light Blue Wall

In Florida, where everyday feels like summer, you’ll be stopping at all the vibrant, colorful walls to snap a few photos. Whether you’re searching for a simple background or a subtle way to brighten neutral attire, a pop-of-color wall like this will make for an incredible photo backdrop.

📍  2 E Plant St, Winter Garden, FL 34787

Centennial Plaza

Centennial Plaza, located in the heart of Downtown Winter Garden, is home to many Insta-worthy photo locations you won’t be able to pass up. The industrial “Centennial Plaza” arch, the white Gazebo draped with stunning purple flowers, and the Orange Trail Fountain. 

📍 101 W Plant St, Winter Garden, FL 34787

Orange Trail Fountain

The Orange Trail fountain, located in the middle of Centennial Plaza, is giving us major Trevi Fountain vibes. From the tall fountain centerpiece to the mosaic tiles along the rim, this is the perfect photo stop for an out-of-the-ordinary Instagram post. 

📍 W Orange Trail (middle walkway of downtown)


There’s no shortage of vibrant wall murals in the downtown Winter Garden area. Scattered throughout the downtown area you’ll find a Florida orange tree mural, a colorful humming bird, and many more. Grab a coffee, your camera, and wander the streets of Winter Garden hunting down the best photo ops. 

📍 99 W Plant St, Winter Garden, FL 34787

Photos by: Aliya Burshan

Insta-Worthy Spots in Winter Garden

Excited about exploring different Insta-worthy spots in Winter Garden? Let us know your favorites by tagging @StuffToDoInOrlando on Instagram and Facebook!

Kailey Boyer

Kailey Boyer

Kailey Boyer is an Arizona native, currently living her best life in Orlando, Florida. She’s passionate about hunting down and sharing all things her beautiful city has to offer. Making the hidden Florida gems accessible to everyone! You can find her exploring Orlando with a camera in hand, typing away in a local coffee shop, or in a packed car heading to the beach.

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